Methyl iodide → HCID 67000076, compound

HRID 558981Notes

Reaction equation

HRID 558981 reaction equation
[C:1](=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][C:12]([NH:14][C:15]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])=[O:13])([CH3:10])([CH3:9])[CH3:8].IC>CN(C=O)C>[CH3:1][O:18][C:17](=[O:19])[C:16]1[CH:20]=[CH:21][CH:22]=[C:23]([F:24])[C:15]=1[NH:14][C:12]([O:11][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 112882942-(tert-Butoxycarbonylamino)-3-fluoro-benzoic acid

Product 1

HCID 67000076HCID 67000076, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of caesium carbonate (1.3 g, 4.0 mmol) in DMF (5.0 ml) was added 2-tert-butoxycarbonylamino-3-fluorobenzoic acid from Example 19A (890 mg, 3.5 mmol) and iodomethane (230 μl, 3.8 mmol). The mixture was stirred for 18 h and evaporated in vacuo. The residue was partitioned between EtOAc and brine and the organic layer was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc;pet. ether 25:75) to give a white solid; yield 680 mg, 72%.

Workup

  1. customevaporated in vacuo
  2. customThe residue was partitioned between EtOAc and brine
  3. customthe organic layer was dried
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography on silica (eluant EtOAc;pet. ether 25:75)
  6. customto give a white solid

Sources & evidence

ORD record
ord-b4577a81d0e441ea88c1b3524d8a95ca
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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